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Unusual Rearrangement by Anodic Oxidation of Cycloalkanones in the Presence of Trifluoroacetic Acid

  • Ikuzo Nishiguchi
Conference paper

Abstract

Anodic oxidation of cyclopentanone and cyclohexanones in a mixed solvent of CF3COOH and CH2C12 containing triethylamine led to unusual rearrangement to give selectively γ-valerolactone and a mixture of γ-and δ-lactones, respectively.

Anodic cleavage of a bond between the carbonyl carbon and the adjacent carbon of cycloalkanones followed by Wagner-Meerwein rearrangement and re-cyclization may be proposed as one of the most plausible reaction mechanisms.

Keywords

Anodic Oxidation Carbonyl Carbon Lithium Perchlorate Sole Product Cyclic Ketone 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Ikuzo Nishiguchi
    • 1
  1. 1.Department of ChemistryNagaoka University of TechnologyNagaoka, NiigataJapan

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